Most of the "what's your opinion of the ... system?" are tainted because most people (obviously excepting Gunni, MaineSail, etc.) have not tried all the options in a variety of conditions. First, in looking at a used boat, the sail quality and replacement is probably not 10% of the purchase price, so it should rank no more than that in your decision. I bought my current C36 having never looked at the sails, expecting them to be the original cheapest quality and ready for replacement -- I gave them no value (Boy, was I right!)
Here's my experience with both Dutchman and Lazy-jacks for coastal cruising / day sailing with a couple or solo. I think that some mainsail dropping aid is needed, and all of them come with some drawbacks, usually in raising sails. All of this assumes you're following instructions (not trying to raise or lower off the wind, and taking time to get the system ready before it is used). Both systems do a good job corralling the sail coming down -- this depends largely on care in setting them up for retrieval. Both systems require loosening before raising and sailing, then re-tightening to recover the sail. On my C36, the Dutchman lets the sail fall off the boom when it is fully down, even when tightened, meaning more physical work to lift it back up to put on the sail cover. If not fully tightened and with the guidelines exactly vertical above the holes, the sail does not fall completely down but gets hung-up on the mono-filament. The Dutchman is more forgiving on raising, and cannot foul the battens. I did experience the "cutting" of the sail cloth when one of the guide rings popped apart, and it was a matter of seconds to get the sail down when I saw it happen, so it's very fast. I plan to replace this system with lazy-jacks this winter, with which I have experience on friends' boats and charters. I like the boom bag system (not possible with Dutchman) because I hate climbing all over the place putting on sail covers when I'm tired after sailing -- the zipper is attractive. I've never had a problem dropping sails into lazy jacks, except in charters where they do not clean the luff track.